Decarbonylative/Acylative Sonogashira Coupling of Biomass-Derived Furandicarbonyl Dichloride: A Route to Unsymmetrically Disubstituted Furans.

Substituted furans serve as pivotal building blocks for pharmaceutical agents and functional materials. In this study, we developed a Cu/Pd-catalyzed decarbonylative/acylative Sonogashira cross-coupling protocol, employing biomass-derived 2,5-furandicarboxylic dichloride and terminal alkynes as reactants, establishing a novel synthetic route for the production of unsymmetrically disubstituted furans. Both alkyl- and aryl-terminal alkynes are amenable to this tunable decarbonylative alkynylation transformation, yielding furan-based alkyne products bearing diverse electron-withdrawing and electron-donating substituents. The incorporated alkyne moiety can undergo further functionalization to afford an array of nitrogen-containing heterocyclic compounds. This study significantly propels the advancement of harnessing biomass-derived feedstocks for the sustainable production of high-value chemicals in the chemical synthesis industry.